KR20070100735A - 약학적 화합물 및 조성물 - Google Patents

약학적 화합물 및 조성물 Download PDF

Info

Publication number: KR20070100735A
Authority: KR; South Korea
Prior art keywords: pharmaceutical composition; levosalbutamol; sulfate; crystalline; propellant
Prior art date: 2004-12-17
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

KR1020077016000A

Other languages

English (en)

Korean (ko)

Inventor

아마르 룰라

지나 말호트라

다르마라즈 람찬드라 라오

라젠드라 나라얀라오 칸칸

알카 차우드하리

Original Assignee

씨아이피엘에이 엘티디.

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2004-12-17

Filing date

2005-12-19

Publication date

2007-10-11

2005-12-19 Application filed by 씨아이피엘에이 엘티디. filed Critical 씨아이피엘에이 엘티디.

2007-10-11 Publication of KR20070100735A publication Critical patent/KR20070100735A/ko

Status Abandoned legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 98
150000001875 compounds Chemical class 0.000 title claims description 21
238000000034 method Methods 0.000 claims abstract description 104
BNPSSFBOAGDEEL-NMFAMCKASA-N 4-[(1r)-2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol;sulfuric acid Chemical group OS(O)(=O)=O.CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=C1.CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=C1 BNPSSFBOAGDEEL-NMFAMCKASA-N 0.000 claims abstract description 62
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 59
229960002052 salbutamol Drugs 0.000 claims abstract description 59
NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims abstract description 58
239000003814 drug Substances 0.000 claims abstract description 46
239000004094 surface-active agent Substances 0.000 claims abstract description 43
150000003839 salts Chemical class 0.000 claims abstract description 37
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 33
238000009472 formulation Methods 0.000 claims abstract description 32
229940079593 drug Drugs 0.000 claims abstract description 30
239000003862 glucocorticoid Substances 0.000 claims abstract description 30
239000003380 propellant Substances 0.000 claims abstract description 30
239000000443 aerosol Substances 0.000 claims abstract description 26
239000012453 solvate Substances 0.000 claims abstract description 24
150000002148 esters Chemical class 0.000 claims abstract description 23
239000006184 cosolvent Substances 0.000 claims abstract description 22
239000000725 suspension Substances 0.000 claims abstract description 18
239000000654 additive Substances 0.000 claims abstract description 13
239000003937 drug carrier Substances 0.000 claims abstract description 13
229940037128 systemic glucocorticoids Drugs 0.000 claims abstract description 13
238000001144 powder X-ray diffraction data Methods 0.000 claims abstract description 12
239000004606 Fillers/Extenders Substances 0.000 claims abstract description 10
229940124597 therapeutic agent Drugs 0.000 claims abstract description 4
NDAUXUAQIAJITI-LBPRGKRZSA-N (R)-salbutamol Chemical compound CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-LBPRGKRZSA-N 0.000 claims description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
230000008569 process Effects 0.000 claims description 38
229950008204 levosalbutamol Drugs 0.000 claims description 37
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
238000002360 preparation method Methods 0.000 claims description 24
208000006673 asthma Diseases 0.000 claims description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 22
LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 21
239000003960 organic solvent Substances 0.000 claims description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
239000013543 active substance Substances 0.000 claims description 18
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 16
235000019404 dichlorodifluoromethane Nutrition 0.000 claims description 16
WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 claims description 16
238000002329 infrared spectrum Methods 0.000 claims description 16
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 16
229960000289 fluticasone propionate Drugs 0.000 claims description 14
-1 sorbitan fatty acid esters Chemical class 0.000 claims description 14
208000023504 respiratory system disease Diseases 0.000 claims description 13
VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims description 12
229960004436 budesonide Drugs 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 12
239000000843 powder Substances 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 11
KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 claims description 11
229950000210 beclometasone dipropionate Drugs 0.000 claims description 11
239000000787 lecithin Substances 0.000 claims description 11
235000010445 lecithin Nutrition 0.000 claims description 11
229940067606 lecithin Drugs 0.000 claims description 11
238000002156 mixing Methods 0.000 claims description 10
239000000047 product Substances 0.000 claims description 10
208000024891 symptom Diseases 0.000 claims description 10
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 claims description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
239000004480 active ingredient Substances 0.000 claims description 9
150000001298 alcohols Chemical class 0.000 claims description 9
230000008602 contraction Effects 0.000 claims description 9
238000011049 filling Methods 0.000 claims description 9
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 9
239000007787 solid Substances 0.000 claims description 9
238000002788 crimping Methods 0.000 claims description 8
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 7
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 7
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 7
239000005642 Oleic acid Substances 0.000 claims description 7
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 7
239000002738 chelating agent Substances 0.000 claims description 7
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 7
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 6
235000014113 dietary fatty acids Nutrition 0.000 claims description 6
239000000194 fatty acid Substances 0.000 claims description 6
229930195729 fatty acid Natural products 0.000 claims description 6
238000010902 jet-milling Methods 0.000 claims description 6
239000008101 lactose Substances 0.000 claims description 6
239000003921 oil Substances 0.000 claims description 6
235000019198 oils Nutrition 0.000 claims description 6
239000000080 wetting agent Substances 0.000 claims description 6
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 5
230000000996 additive effect Effects 0.000 claims description 5
229940112141 dry powder inhaler Drugs 0.000 claims description 5
229940041682 inhalant solution Drugs 0.000 claims description 5
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 4
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 claims description 4
230000001476 alcoholic effect Effects 0.000 claims description 4
239000000890 drug combination Substances 0.000 claims description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 4
229920001223 polyethylene glycol Polymers 0.000 claims description 4
ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 claims description 4
HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims description 3
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Polymers OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 3
OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims description 3
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 3
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 3
HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 3
229920002307 Dextran Polymers 0.000 claims description 3
229930091371 Fructose Natural products 0.000 claims description 3
239000005715 Fructose Substances 0.000 claims description 3
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims description 3
229930195725 Mannitol Natural products 0.000 claims description 3
239000002202 Polyethylene glycol Substances 0.000 claims description 3
PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 3
229920002472 Starch Polymers 0.000 claims description 3
235000021355 Stearic acid Nutrition 0.000 claims description 3
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 3
229930006000 Sucrose Natural products 0.000 claims description 3
HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 claims description 3
HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 claims description 3
HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 3
PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 3
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 3
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 3
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 3
GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 claims description 3
239000004067 bulking agent Substances 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
150000002016 disaccharides Chemical class 0.000 claims description 3
239000008103 glucose Substances 0.000 claims description 3
150000004676 glycans Chemical class 0.000 claims description 3
239000000594 mannitol Substances 0.000 claims description 3
235000010355 mannitol Nutrition 0.000 claims description 3
150000002772 monosaccharides Chemical group 0.000 claims description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
239000002798 polar solvent Substances 0.000 claims description 3
229920001282 polysaccharide Polymers 0.000 claims description 3
239000005017 polysaccharide Substances 0.000 claims description 3
238000001556 precipitation Methods 0.000 claims description 3
239000008107 starch Substances 0.000 claims description 3
235000019698 starch Nutrition 0.000 claims description 3
239000008117 stearic acid Substances 0.000 claims description 3
239000005720 sucrose Substances 0.000 claims description 3
235000000346 sugar Nutrition 0.000 claims description 3
150000005846 sugar alcohols Chemical class 0.000 claims description 3
239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 claims description 2
JNYAEWCLZODPBN-UHFFFAOYSA-N 2-(1,2-dihydroxyethyl)oxolane-3,4-diol Polymers OCC(O)C1OCC(O)C1O JNYAEWCLZODPBN-UHFFFAOYSA-N 0.000 claims description 2
RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 claims description 2
VNVNZKCCDVFGAP-FPDJQMMJSA-N 4-[(1r)-2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol;(2r,3r)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=C1.CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=C1 VNVNZKCCDVFGAP-FPDJQMMJSA-N 0.000 claims description 2
OWNWYCOLFIFTLK-YDALLXLXSA-N 4-[(1r)-2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol;hydron;chloride Chemical compound Cl.CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=C1 OWNWYCOLFIFTLK-YDALLXLXSA-N 0.000 claims description 2
QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 claims description 2
239000011786 L-ascorbyl-6-palmitate Substances 0.000 claims description 2
229920001213 Polysorbate 20 Polymers 0.000 claims description 2
NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 claims description 2
239000004147 Sorbitan trioleate Substances 0.000 claims description 2
PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 claims description 2
PRXRUNOAOLTIEF-XDTJCZEISA-N [2-[(2r,3s,4r)-4-hydroxy-3-[(z)-octadec-9-enoyl]oxyoxolan-2-yl]-2-[(z)-octadec-9-enoyl]oxyethyl] (z)-octadec-9-enoate Polymers CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@@H](O)[C@@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-XDTJCZEISA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
JBDGDEWWOUBZPM-XYPYZODXSA-N ambroxol Chemical compound NC1=C(Br)C=C(Br)C=C1CN[C@@H]1CC[C@@H](O)CC1 JBDGDEWWOUBZPM-XYPYZODXSA-N 0.000 claims description 2
229960005174 ambroxol Drugs 0.000 claims description 2
235000010385 ascorbyl palmitate Nutrition 0.000 claims description 2
229960000541 cetyl alcohol Drugs 0.000 claims description 2
YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 claims description 2
229960001927 cetylpyridinium chloride Drugs 0.000 claims description 2
239000007859 condensation product Substances 0.000 claims description 2
239000002285 corn oil Substances 0.000 claims description 2
235000005687 corn oil Nutrition 0.000 claims description 2
235000012343 cottonseed oil Nutrition 0.000 claims description 2
239000002385 cottonseed oil Substances 0.000 claims description 2
UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 claims description 2
125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims description 2
229940068939 glyceryl monolaurate Drugs 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
150000002430 hydrocarbons Chemical class 0.000 claims description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
229940057995 liquid paraffin Drugs 0.000 claims description 2
230000007774 longterm Effects 0.000 claims description 2
229960003511 macrogol Drugs 0.000 claims description 2
239000002480 mineral oil Substances 0.000 claims description 2
RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 claims description 2
229940049964 oleate Drugs 0.000 claims description 2
239000004006 olive oil Substances 0.000 claims description 2
235000008390 olive oil Nutrition 0.000 claims description 2
150000003904 phospholipids Chemical class 0.000 claims description 2
229920000642 polymer Polymers 0.000 claims description 2
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims description 2
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 2
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 2
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 2
229940068977 polysorbate 20 Drugs 0.000 claims description 2
229940068968 polysorbate 80 Drugs 0.000 claims description 2
229920000053 polysorbate 80 Polymers 0.000 claims description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 2
239000001267 polyvinylpyrrolidone Substances 0.000 claims description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 2
WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 claims description 2
JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 claims description 2
229950004959 sorbitan oleate Drugs 0.000 claims description 2
235000019337 sorbitan trioleate Nutrition 0.000 claims description 2
PRXRUNOAOLTIEF-WUOFIQDXSA-N sorbitan trioleate Polymers CCCCCCCC\C=C\CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C\CCCCCCCC)C1OCC(O)C1OC(=O)CCCCCCC\C=C\CCCCCCCC PRXRUNOAOLTIEF-WUOFIQDXSA-N 0.000 claims description 2
229960000391 sorbitan trioleate Drugs 0.000 claims description 2
235000020238 sunflower seed Nutrition 0.000 claims description 2
229960000278 theophylline Drugs 0.000 claims description 2
150000003611 tocopherol derivatives Chemical class 0.000 claims description 2
150000003626 triacylglycerols Chemical class 0.000 claims description 2
PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims description 2
229940117972 triolein Drugs 0.000 claims description 2
JJCCTHHSPPINEI-MQWKRIRWSA-N 2,3-dihydroxypropyl (2s)-2,6-diaminohexanoate Chemical compound NCCCC[C@H](N)C(=O)OCC(O)CO JJCCTHHSPPINEI-MQWKRIRWSA-N 0.000 claims 1
239000008135 aqueous vehicle Substances 0.000 claims 1
150000002191 fatty alcohols Chemical class 0.000 claims 1
125000003827 glycol group Chemical group 0.000 claims 1
229960001361 ipratropium bromide Drugs 0.000 claims 1
KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 claims 1
239000004615 ingredient Substances 0.000 abstract description 16
229910021653 sulphate ion Inorganic materials 0.000 abstract description 4
YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 description 15
235000019441 ethanol Nutrition 0.000 description 15
238000000634 powder X-ray diffraction Methods 0.000 description 15
230000000694 effects Effects 0.000 description 13
239000002245 particle Substances 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
102000016966 beta-2 Adrenergic Receptors Human genes 0.000 description 9
108010014499 beta-2 Adrenergic Receptors Proteins 0.000 description 9
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 8
229940124630 bronchodilator Drugs 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
239000002002 slurry Substances 0.000 description 8
238000000227 grinding Methods 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000048 adrenergic agonist Substances 0.000 description 6
229940126157 adrenergic receptor agonist Drugs 0.000 description 6
NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical class C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 description 6
238000010586 diagram Methods 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
229940092705 beclomethasone Drugs 0.000 description 5
239000003246 corticosteroid Substances 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
UCTWMZQNUQWSLP-UHFFFAOYSA-N Adrenaline Natural products CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
239000000168 bronchodilator agent Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000011928 denatured alcohol Substances 0.000 description 4
210000004072 lung Anatomy 0.000 description 4
239000006199 nebulizer Substances 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
239000008249 pharmaceutical aerosol Substances 0.000 description 4
230000003389 potentiating effect Effects 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
NDAUXUAQIAJITI-GFCCVEGCSA-N 4-[(1s)-2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound CC(C)(C)NC[C@@H](O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-GFCCVEGCSA-N 0.000 description 3
208000000059 Dyspnea Diseases 0.000 description 3
206010013975 Dyspnoeas Diseases 0.000 description 3
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
238000002441 X-ray diffraction Methods 0.000 description 3
230000009471 action Effects 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
230000003182 bronchodilatating effect Effects 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001914 filtration Methods 0.000 description 3
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical class C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 description 3
150000002334 glycols Chemical class 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
239000008213 purified water Substances 0.000 description 3
210000002460 smooth muscle Anatomy 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 2
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
BLUGYPPOFIHFJS-UUFHNPECSA-N (2s)-n-[(2s)-1-[[(3r,4s,5s)-3-methoxy-1-[(2s)-2-[(1r,2r)-1-methoxy-2-methyl-3-oxo-3-[[(1s)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino]propyl]pyrrolidin-1-yl]-5-methyl-1-oxoheptan-4-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]-3-methyl-2-(methylamino)butanamid Chemical compound CN[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)[C@H](OC)CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@H](C=1SC=CN=1)CC1=CC=CC=C1 BLUGYPPOFIHFJS-UUFHNPECSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
208000007934 ACTH-independent macronodular adrenal hyperplasia Diseases 0.000 description 2
229930003347 Atropine Natural products 0.000 description 2
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
229940121948 Muscarinic receptor antagonist Drugs 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
102000004257 Potassium Channel Human genes 0.000 description 2
GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000012190 activator Substances 0.000 description 2
210000005091 airway smooth muscle Anatomy 0.000 description 2
229940035676 analgesics Drugs 0.000 description 2
239000000730 antalgic agent Substances 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
239000000043 antiallergic agent Substances 0.000 description 2
239000000739 antihistaminic agent Substances 0.000 description 2
229940125715 antihistaminic agent Drugs 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
235000006708 antioxidants Nutrition 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 2
229960000396 atropine Drugs 0.000 description 2
239000002585 base Substances 0.000 description 2
229960000686 benzalkonium chloride Drugs 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
229940124748 beta 2 agonist Drugs 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 2
239000000812 cholinergic antagonist Substances 0.000 description 2
239000008139 complexing agent Substances 0.000 description 2
229960001334 corticosteroids Drugs 0.000 description 2
239000013078 crystal Substances 0.000 description 2
229960000676 flunisolide Drugs 0.000 description 2
229960002714 fluticasone Drugs 0.000 description 2
229960002848 formoterol Drugs 0.000 description 2
BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 description 2
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
230000004941 influx Effects 0.000 description 2
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
239000007951 isotonicity adjuster Substances 0.000 description 2
230000012241 membrane hyperpolarization Effects 0.000 description 2
LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 2
229940071648 metered dose inhaler Drugs 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
210000000663 muscle cell Anatomy 0.000 description 2
229960002657 orciprenaline Drugs 0.000 description 2
239000008188 pellet Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
108020001213 potassium channel Proteins 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000002441 reversible effect Effects 0.000 description 2
229960004017 salmeterol Drugs 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000007921 spray Substances 0.000 description 2
230000001954 sterilising effect Effects 0.000 description 2
238000004659 sterilization and disinfection Methods 0.000 description 2
150000003431 steroids Chemical class 0.000 description 2
239000000021 stimulant Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
150000008163 sugars Chemical class 0.000 description 2
229960000195 terbutaline Drugs 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
AKNNEGZIBPJZJG-MSOLQXFVSA-N (-)-noscapine Chemical compound CN1CCC2=CC=3OCOC=3C(OC)=C2[C@@H]1[C@@H]1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-MSOLQXFVSA-N 0.000 description 1
UBLVUWUKNHKCJJ-ZSCHJXSPSA-N (2s)-2,6-diaminohexanoic acid;1,3-dimethyl-7h-purine-2,6-dione Chemical compound NCCCC[C@H](N)C(O)=O.O=C1N(C)C(=O)N(C)C2=C1NC=N2 UBLVUWUKNHKCJJ-ZSCHJXSPSA-N 0.000 description 1
WRRSFOZOETZUPG-FFHNEAJVSA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;hydrate Chemical compound O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC WRRSFOZOETZUPG-FFHNEAJVSA-N 0.000 description 1
YZAZXIUFBCPZGB-QZOPMXJLSA-N (z)-octadec-9-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O YZAZXIUFBCPZGB-QZOPMXJLSA-N 0.000 description 1
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
HDIFHQMREAYYJW-FMIVXFBMSA-N 2,3-dihydroxypropyl (e)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C\CCCCCCCC(=O)OCC(O)CO HDIFHQMREAYYJW-FMIVXFBMSA-N 0.000 description 1
CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
YREYLAVBNPACJM-UHFFFAOYSA-N 2-(tert-butylamino)-1-(2-chlorophenyl)ethanol Chemical compound CC(C)(C)NCC(O)C1=CC=CC=C1Cl YREYLAVBNPACJM-UHFFFAOYSA-N 0.000 description 1
NVOYVOBDTVTBDX-AGUVMIOSSA-N 8g15t83e6i Chemical compound C1([C@@H](CO)C(=O)OC2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)CC)=CC=CC=C1 NVOYVOBDTVTBDX-AGUVMIOSSA-N 0.000 description 1
208000020053 Abnormal inflammatory response Diseases 0.000 description 1
208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
102100039705 Beta-2 adrenergic receptor Human genes 0.000 description 1
101710152983 Beta-2 adrenergic receptor Proteins 0.000 description 1
208000009079 Bronchial Spasm Diseases 0.000 description 1
208000014181 Bronchial disease Diseases 0.000 description 1
206010006482 Bronchospasm Diseases 0.000 description 1
229930186147 Cephalosporin Natural products 0.000 description 1
208000017667 Chronic Disease Diseases 0.000 description 1
MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
IJVCSMSMFSCRME-KBQPJGBKSA-N Dihydromorphine Chemical compound O([C@H]1[C@H](CC[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O IJVCSMSMFSCRME-KBQPJGBKSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
102400000321 Glucagon Human genes 0.000 description 1
108060003199 Glucagon Proteins 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
102000004877 Insulin Human genes 0.000 description 1
108090001061 Insulin Proteins 0.000 description 1
HUYWAWARQUIQLE-UHFFFAOYSA-N Isoetharine Chemical compound CC(C)NC(CC)C(O)C1=CC=C(O)C(O)=C1 HUYWAWARQUIQLE-UHFFFAOYSA-N 0.000 description 1
ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 description 1
150000000994 L-ascorbates Chemical class 0.000 description 1
208000019693 Lung disease Diseases 0.000 description 1
208000007101 Muscle Cramp Diseases 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
208000027771 Obstructive airways disease Diseases 0.000 description 1
206010030111 Oedema mucosal Diseases 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
VQDBNKDJNJQRDG-UHFFFAOYSA-N Pirbuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=N1 VQDBNKDJNJQRDG-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
206010036595 Premature delivery Diseases 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
239000004098 Tetracycline Substances 0.000 description 1
DXEXNWDGDYUITL-FXSSSKFRSA-N Tipredane Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1CC[C@@](SC)(SCC)[C@@]1(C)C[C@@H]2O DXEXNWDGDYUITL-FXSSSKFRSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000011149 active material Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000000556 agonist Substances 0.000 description 1
208000037883 airway inflammation Diseases 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
AKNNEGZIBPJZJG-UHFFFAOYSA-N alpha-noscapine Natural products CN1CCC2=CC=3OCOC=3C(OC)=C2C1C1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229960003556 aminophylline Drugs 0.000 description 1
FQPFAHBPWDRTLU-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=C1NC=N2.O=C1N(C)C(=O)N(C)C2=C1NC=N2 FQPFAHBPWDRTLU-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000000954 anitussive effect Effects 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
229960005475 antiinfective agent Drugs 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
239000003434 antitussive agent Substances 0.000 description 1
229940124584 antitussives Drugs 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
229960003060 bambuterol Drugs 0.000 description 1
ANZXOIAKUNOVQU-UHFFFAOYSA-N bambuterol Chemical compound CN(C)C(=O)OC1=CC(OC(=O)N(C)C)=CC(C(O)CNC(C)(C)C)=C1 ANZXOIAKUNOVQU-UHFFFAOYSA-N 0.000 description 1
230000008901 benefit Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
229960004365 benzoic acid Drugs 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
229960004217 benzyl alcohol Drugs 0.000 description 1
229940125388 beta agonist Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
ZDIGNSYAACHWNL-UHFFFAOYSA-N brompheniramine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Br)C=C1 ZDIGNSYAACHWNL-UHFFFAOYSA-N 0.000 description 1
230000010083 bronchial hyperresponsiveness Effects 0.000 description 1
150000004648 butanoic acid derivatives Chemical class 0.000 description 1
239000011575 calcium Substances 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000007894 caplet Substances 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
229960003821 choline theophyllinate Drugs 0.000 description 1
230000001713 cholinergic effect Effects 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
229960004126 codeine Drugs 0.000 description 1
OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Natural products C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229960004544 cortisone Drugs 0.000 description 1
IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
229960003957 dexamethasone Drugs 0.000 description 1
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 1
229960004166 diltiazem Drugs 0.000 description 1
IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000013583 drug formulation Substances 0.000 description 1
229960001484 edetic acid Drugs 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
229960002179 ephedrine Drugs 0.000 description 1
OFKDAAIKGIBASY-VFGNJEKYSA-N ergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C3=CC=CC4=NC=C([C]34)C2)=C1)C)C1=CC=CC=C1 OFKDAAIKGIBASY-VFGNJEKYSA-N 0.000 description 1
229960004943 ergotamine Drugs 0.000 description 1
XCGSFFUVFURLIX-UHFFFAOYSA-N ergotaminine Natural products C1=C(C=2C=CC=C3NC=C(C=23)C2)C2N(C)CC1C(=O)NC(C(N12)=O)(C)OC1(O)C1CCCN1C(=O)C2CC1=CC=CC=C1 XCGSFFUVFURLIX-UHFFFAOYSA-N 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
239000003172 expectorant agent Substances 0.000 description 1
239000003925 fat Substances 0.000 description 1
229960001022 fenoterol Drugs 0.000 description 1
LSLYOANBFKQKPT-UHFFFAOYSA-N fenoterol Chemical compound C=1C(O)=CC(O)=CC=1C(O)CNC(C)CC1=CC=C(O)C=C1 LSLYOANBFKQKPT-UHFFFAOYSA-N 0.000 description 1
229960002428 fentanyl Drugs 0.000 description 1
IVLVTNPOHDFFCJ-UHFFFAOYSA-N fentanyl citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 IVLVTNPOHDFFCJ-UHFFFAOYSA-N 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
229940033835 flonase Drugs 0.000 description 1
229940085861 flovent Drugs 0.000 description 1
239000012458 free base Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000007789 gas Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 description 1
229960004666 glucagon Drugs 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000007970 homogeneous dispersion Substances 0.000 description 1
229940125697 hormonal agent Drugs 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
229960000890 hydrocortisone Drugs 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
238000002664 inhalation therapy Methods 0.000 description 1
229940125369 inhaled corticosteroids Drugs 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229940125396 insulin Drugs 0.000 description 1
229960001268 isoetarine Drugs 0.000 description 1
229960001317 isoprenaline Drugs 0.000 description 1
229960004958 ketotifen Drugs 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
239000003509 long acting drug Substances 0.000 description 1
229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 description 1
238000005461 lubrication Methods 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
150000004701 malic acid derivatives Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
HNJJXZKZRAWDPF-UHFFFAOYSA-N methapyrilene Chemical compound C=1C=CC=NC=1N(CCN(C)C)CC1=CC=CS1 HNJJXZKZRAWDPF-UHFFFAOYSA-N 0.000 description 1
229960001869 methapyrilene Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000003607 modifier Substances 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
230000000510 mucolytic effect Effects 0.000 description 1
229940066491 mucolytics Drugs 0.000 description 1
PLPRGLOFPNJOTN-UHFFFAOYSA-N narcotine Natural products COc1ccc2C(OC(=O)c2c1OC)C3Cc4c(CN3C)cc5OCOc5c4OC PLPRGLOFPNJOTN-UHFFFAOYSA-N 0.000 description 1
229960004398 nedocromil Drugs 0.000 description 1
RQTOOFIXOKYGAN-UHFFFAOYSA-N nedocromil Chemical compound CCN1C(C(O)=O)=CC(=O)C2=C1C(CCC)=C1OC(C(O)=O)=CC(=O)C1=C2 RQTOOFIXOKYGAN-UHFFFAOYSA-N 0.000 description 1
239000002547 new drug Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229960004708 noscapine Drugs 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
RLANKEDHRWMNRO-UHFFFAOYSA-M oxtriphylline Chemical compound C[N+](C)(C)CCO.O=C1N(C)C(=O)N(C)C2=C1[N-]C=N2 RLANKEDHRWMNRO-UHFFFAOYSA-M 0.000 description 1
239000003002 pH adjusting agent Substances 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
230000007310 pathophysiology Effects 0.000 description 1
230000035515 penetration Effects 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 1
229960004448 pentamidine Drugs 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229960001802 phenylephrine Drugs 0.000 description 1
SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
229960000395 phenylpropanolamine Drugs 0.000 description 1
DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 description 1
229960005414 pirbuterol Drugs 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
235000010241 potassium sorbate Nutrition 0.000 description 1
239000004302 potassium sorbate Substances 0.000 description 1
229940069338 potassium sorbate Drugs 0.000 description 1
239000002243 precursor Substances 0.000 description 1
229960005205 prednisolone Drugs 0.000 description 1
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229960002720 reproterol Drugs 0.000 description 1
WVLAAKXASPCBGT-UHFFFAOYSA-N reproterol Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2N=CN1CCCNCC(O)C1=CC(O)=CC(O)=C1 WVLAAKXASPCBGT-UHFFFAOYSA-N 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
229960001457 rimiterol Drugs 0.000 description 1
IYMMESGOJVNCKV-SKDRFNHKSA-N rimiterol Chemical compound C([C@@H]1[C@@H](O)C=2C=C(O)C(O)=CC=2)CCCN1 IYMMESGOJVNCKV-SKDRFNHKSA-N 0.000 description 1
230000000391 smoking effect Effects 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
229960003885 sodium benzoate Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000000527 sonication Methods 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
230000009967 tasteless effect Effects 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
229940040944 tetracyclines Drugs 0.000 description 1
LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical compound O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 description 1
229940110309 tiotropium Drugs 0.000 description 1
229950001669 tipredane Drugs 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
229960002117 triamcinolone acetonide Drugs 0.000 description 1
YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
229960000859 tulobuterol Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical class CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Images

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/0078—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a nebulizer such as a jet nebulizer, ultrasonic nebulizer, e.g. in the form of aqueous drug solutions or dispersions
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/0075—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/12—Aerosols; Foams
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/56—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups
- C07C215/58—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
- C07C215/60—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain the chain having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Epidemiology (AREA)
Pulmonology (AREA)
Otolaryngology (AREA)
Dispersion Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Emergency Medicine (AREA)
General Chemical & Material Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

KR1020077016000A 2004-12-17 2005-12-19 약학적 화합물 및 조성물 Abandoned KR20070100735A (ko)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
IN1356MU2004		2004-12-17
IN1356/MUM/2004		2004-12-17
IN40/MUM/2005		2005-01-14
IN40MU2005		2005-01-14
IN343MU2005		2005-03-24
IN343/MUM/2005		2005-03-24

Publications (1)

Publication Number	Publication Date
KR20070100735A true KR20070100735A (ko)	2007-10-11

Family

ID=36091333

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
KR1020077016000A Abandoned KR20070100735A (ko)	2004-12-17	2005-12-19	약학적 화합물 및 조성물

Country Status (11)

Country	Link
US (1)	US20090263333A1 (fr)
EP (2)	EP2311793A1 (fr)
JP (1)	JP2008524195A (fr)
KR (1)	KR20070100735A (fr)
AU (1)	AU2005315337B2 (fr)
BR (1)	BRPI0517204A (fr)
CA (1)	CA2591406A1 (fr)
IL (1)	IL183986A0 (fr)
MX (1)	MX2007007378A (fr)
NZ (1)	NZ555500A (fr)
WO (1)	WO2006064283A1 (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1809243B2 (fr)	2004-07-02	2022-06-08	Boehringer Ingelheim International GmbH	Formulations de suspensions aerosol contenant tg 227 ea en tant qu'agent propulseur
DE102006017320A1 (de)	2006-04-11	2007-10-18	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Aerosolsuspensionsformulierungen mit TG 227 ea oder TG 134 a als Treibmittel
US20070282010A1 (en)	2006-05-30	2007-12-06	Bridge Pharma, Inc.	Methods of Accelerating Muscle Growth, Decreasing Fat Deposits and Improving Feed Efficiency in Livestock Animals
MX2010005036A (es) *	2007-11-07	2010-05-27	Astrazeneca Ab	Formulaciones de polvo seco que comprenden derivados del acido ascorbico.
AU2008331928B2 (en)	2007-12-03	2012-08-16	Bridge Pharma, Inc.	Use of RR/SR-ractopamine
PT105058B (pt) *	2010-04-21	2013-04-17	Hovione Farmaciencia S A	Processo para processamento de partículas de ingredientes activos farmacêuticos
IT1399912B1 (it) *	2010-04-29	2013-05-09	Lundbeck Pharmaceuticals Italy S Pa	Processo di preparazione di ritodrina cloridrato.
ES2729549T3 (es) *	2011-08-02	2019-11-04	Alfasigma Spa	Composición farmacéutica de avidina oxidada adecuada para la inhalación
WO2013140120A1 (fr) *	2012-03-22	2013-09-26	Cipla Limited	Formes solvatées de glycérol de (r)-2-[[[3-methyl-4(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl]sulphinyl]-lh-benzimidazole
CA2930170A1 (fr) *	2013-11-22	2015-05-28	Teva Branded Pharmaceutical Products R&D, Inc.	Medicament inhalable
TN2016000259A1 (en)	2016-06-27	2017-10-06	Rekik Raouf	Salbutamol (albuterol) eye protective medicament.
EP3666254B1 (fr)	2017-08-11	2024-12-04	Amorepacific Corporation	Composition pharmaceutique contenant un (r)-n-[1-(3,5-difluoro-4-méthanesulfonylamino-phényl)-éthyl]-3-(2-propyl-6-trifluorométhyl-pyridin-3-yl)-acrylamide
KR102518632B1 (ko)	2018-04-18	2023-04-06	(주)아모레퍼시픽	(r)-n-[1-(3,5-다이플루오로-4-메테인설폰일아미노-페닐)-에틸]-3-(2-프로필-6-트라이플루오로메틸-피리딘-3-일)-아크릴아마이드를 함유하는 약학 조성물
EP3860580A4 (fr) *	2018-10-01	2022-07-20	Kindeva Drug Delivery L.P.	Formulation et cartouches d'aérosol, inhalateurs et analogues contenant la formulation
CN118948813B (zh) *	2024-08-08	2025-03-18	山东中医药大学附属医院	一种支气管扩张剂沙丁胺醇气雾剂及其制备方法

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CY1291A (en)	1980-02-15	1985-10-18	Glaxo Group Ltd	Androstane 17 beta carbothioates
US5362755A (en)	1990-01-05	1994-11-08	Sepracor, Inc.	Method for treating asthma using optically pure (R)-albuterol
IL104068A (en)	1991-12-12	1998-10-30	Glaxo Group Ltd	Surfactant-free pharmaceutical aerosol formulation comprising 1,1,1,2-tetrafluoroethane or 1,1,1,2,3,3,3-heptafluoro-n- propane as propellant
US5545745A (en)	1994-05-23	1996-08-13	Sepracor, Inc.	Enantioselective preparation of optically pure albuterol
US6013245A (en)	1995-01-26	2000-01-11	Glaxo Group Limited	Aerosol formulation containing beclomethasone dipropionate and 1,1,1,2,3,3,3-heptafluoro-n-propane as propellant
WO1996032151A1 (fr) *	1995-04-14	1996-10-17	Glaxo Wellcome Inc.	Inhalateur doseur de propionate fluticasone
SE9700135D0 (sv) *	1997-01-20	1997-01-20	Astra Ab	New formulation
CN1144582C (zh) *	2000-11-28	2004-04-07	中国药科大学	治疗呼吸系统疾病的无氟里昂药用气雾剂
GB0030171D0 (en)	2000-12-11	2001-01-24	Cipla Ltd	Process for preparing isomers of salbutamol
NO315264B1 (no)	2001-01-23	2003-08-11	Tomra Systems Asa	Deteksjonssystem
US6702997B2 (en)	2001-10-26	2004-03-09	Dey, L.P.	Albuterol inhalation solution, system, kit and method for relieving symptoms of pediatric asthma
CN100432044C (zh)	2002-09-13	2008-11-12	苏州君宁新药开发中心有限公司	左旋沙丁胺醇制备新工艺
PT1572622E (pt)	2002-12-10	2006-08-31	Sepracor Inc	Sal de levalbuterol

2005
- 2005-12-19 EP EP10184848A patent/EP2311793A1/fr not_active Withdrawn
- 2005-12-19 US US11/721,866 patent/US20090263333A1/en not_active Abandoned
- 2005-12-19 CA CA002591406A patent/CA2591406A1/fr not_active Abandoned
- 2005-12-19 BR BRPI0517204-7A patent/BRPI0517204A/pt not_active IP Right Cessation
- 2005-12-19 EP EP05843722A patent/EP1828100A1/fr not_active Withdrawn
- 2005-12-19 WO PCT/GB2005/004935 patent/WO2006064283A1/fr not_active Ceased
- 2005-12-19 JP JP2007546199A patent/JP2008524195A/ja active Pending
- 2005-12-19 NZ NZ555500A patent/NZ555500A/en not_active IP Right Cessation
- 2005-12-19 KR KR1020077016000A patent/KR20070100735A/ko not_active Abandoned
- 2005-12-19 MX MX2007007378A patent/MX2007007378A/es active IP Right Grant
- 2005-12-19 AU AU2005315337A patent/AU2005315337B2/en not_active Ceased
2007
- 2007-06-17 IL IL183986A patent/IL183986A0/en unknown

Also Published As

Publication number	Publication date
MX2007007378A (es)	2007-08-14
EP1828100A1 (fr)	2007-09-05
EP2311793A1 (fr)	2011-04-20
CA2591406A1 (fr)	2006-06-22
AU2005315337A1 (en)	2006-06-22
US20090263333A1 (en)	2009-10-22
WO2006064283A1 (fr)	2006-06-22
JP2008524195A (ja)	2008-07-10
NZ555500A (en)	2010-09-30
AU2005315337B2 (en)	2012-07-05
BRPI0517204A (pt)	2008-09-30
IL183986A0 (en)	2007-10-31

Publication	Publication Date	Title
AU2003260754B2 (en)	2009-12-03	Pharmaceutical products and compositions comprising specific anticholinergic agents, beta-2 agonists and corticosteroids
US9050267B2 (en)	2015-06-09	Dry powder formulations of particles that contain two or more active ingredients for treating obstructive or inflammatory airways diseases
AU2005315337B2 (en)	2012-07-05	Pharmaceutical compounds and compositions
AU2005281511B2 (en)	2011-03-31	Pharmaceutical composition comprising an isomer of a betamimetic agent and an anti-cholinergic agent
JP2018199684A (ja)	2018-12-20	Ｒ（＋）ブデソニド及び１以上の気管支拡張剤を含む医薬組成物
JP2002536408A (ja)	2002-10-29	フォルモテロールとチオトロピウム塩の組合わせ
CN101801378A (zh)	2010-08-11	治疗药物的新型组合
RU2440972C2 (ru)	2012-01-27	Кристаллический сульфат левосальбутамола, способ его получения и фармацевтическая композиция, содержащая его
ZA200704378B (en)	2008-07-30	Pharmaceutical compounds and compositions
RU2457832C2 (ru)	2012-08-10	Состав на основе тровентола
ZA200501703B (en)	2005-09-06	Pharmaceutical products and compositions comprising specific anticholinergic agents, beta-2-agonists and corti-costeroids.

Legal Events

Date	Code	Title	Description
2007-07-13	PA0105	International application	Patent event date: 20070713 Patent event code: PA01051R01D Comment text: International Patent Application
2007-10-11	PG1501	Laying open of application
2010-12-17	A201	Request for examination
2010-12-17	PA0201	Request for examination	Patent event code: PA02012R01D Patent event date: 20101217 Comment text: Request for Examination of Application
2012-08-22	PE0902	Notice of grounds for rejection	Comment text: Notification of reason for refusal Patent event date: 20120822 Patent event code: PE09021S01D
2013-03-22	E701	Decision to grant or registration of patent right
2013-03-22	PE0701	Decision of registration	Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20130322
2013-12-23	PC1904	Unpaid initial registration fee